HowAboutWe’s Brian Schechter on WorkFlowy, Rdio, and the Ringtone He’s Saving for His Future Girlfriend

When HowAboutWe first launched in 2010, it looked to disrupt the online-dating business by matching singles based on what they wanted to do off-line. By partnering with existing (and influential) media brands, co-founders, best friends, and former high-school teachers Brian Schechter and Aaron Schildkrout successfully changed the digital dating game—attracting 1.5 million users and ostensibly paving the way for a new wave of dating start-ups like Coffee Meets Bagel and Sparkology. Since then, co-C.E.O.’s Schechter and Schildkrout have attempted to grow their first business by expanding the brand with HowAboutWe for Couples and most recently The Date Report—securing another $4.2 million of new venture capital in the process. We spoke to the New York–based Schechter about life and love on his iPhone 5.

Phone: Black iPhone 5.

Case: None. “I have no excuse for that one.”

Background: Black. “I like to keep it simple.”

Ringtone: Yes. “I actually really like the new i0S 7 ringtones. Aaron’s [Schildkrout] mother gets the FogHorn. Scott—my best friend from high school and our creative director—gets the Cricket. I’m saving the new Radiate for my next girlfriend.”

Last app used:WorkFlowy. “As far as to-do lists are concerned, I love Workflowy’s clean, endless-listing functionality, and it always syncs just right. I’ve essentially gotten my entire team on it, and we all share our docs to stay in sync. It’s kind of replacing the random Google Doc.”

Currently obsessed with:Landcam and Glitche. “I’ve been on a photo-app kick lately. [These] are my favorite. You can create fun—sometimes beautiful and sometimes insane—media snippets so easily with these apps.”

Last download:Tumblr. “I know I’m late to the game with this one, but I recently shared an Uber ride with a Tumblr employee, who set me up with amazing people to follow. Organizing The Soup is the best.”

Favorite mobile game:Connect Four. “I love that game. I’m way better at Connect Four than chess.”

Best-designed app on his phone:Rdio. “I think [its] design and user interface is incredible. I love how the app showcases album artwork in a way that seamlessly integrates new-school digital streaming and an old-school appreciation for music’s analog, visual components.”

Voicemail greeting? No. “What’s voicemail? To be honest, I never listen to voicemails. So if there’s anything there, it’d be an automated prompt.”

Clean inbox? Yes. “Gmail app with priority inbox. Period. I read and respond to most, if not all, of my priority e-mails throughout the day via the Gmail app and clean up/tackle the rest at night. I get to Inbox Zero most nights.”

Text or call? Text. “I prefer to text because it’s faster, easier, and people are much more accepting of shorthand. It’s also much more conducive to multi-tasking, which I do a lot of. That’s not to say I don’t make my fair share of phone calls—today I’ve had five so far. But if I have a choice, it’s texting, hands down.”

Remaining battery: 75 percent. “I’ve been at my desk for a decent chunk of time, so I was able to charge it. Since I’m always checking e-mail and working on my phone while running to meetings, my phone dies 18 times a day. It feels like I’m always recharging.”